European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 1

Early View (Online Version of Record published before inclusion in an issue)

Editor: Haymo Ross, Deputy Editor: Susan Wilkinson

Impact Factor: 3.154

ISI Journal Citation Reports © Ranking: 2013: 14/58 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

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  1. 1 - 60
  1. Full Papers

    1. Conformation Analysis

      Triphenylacetic Acid Amides: Molecular Propellers with Induced Chirality

      Natalia Prusinowska, Wioletta Bendzińska-Berus, Maciej Jelecki, Urszula Rychlewska and Marcin Kwit

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403182

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      Weak but cooperative intramolecular interactions, either CH···O hydrogen bonds or local CH/CO dipole/dipole interactions, play a key role in the process of spectacular chirality transfer in triphenylacetamides.

    2. Natural Products

      Spirangien Derivatives from the Myxobacterium Sorangium cellulosum: Isolation, Structure Elucidation, and Biological Activity

      Nicole Bruns, Wera Collisi, Steffen Bernecker, Marc Stadler, Christian Richter, Harald Schwalbe and Markus Kalesse

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403353

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      Eleven new spirangien derivatives have been isolated from the myxobacterium Sorangium cellulosum. The structures were elucidated by MS and various NMR methods. We used Murata's method and statistical analysis of the PKS gene cluster based on profile hidden Markov models to determine their configurations. All the spirangien derivatives showed high cytotoxicities against two cancer cell lines.

    3. Amination of Flavones

      Buchwald–Hartwig Reactions of Monohaloflavones

      Krisztina Kónya, Dávid Pajtás, Attila Kiss-Szikszai and Tamás Patonay

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403108

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      A new and efficient approach to (substituted) aminoflavones and hybrids of flavones and amino acids using Buchwald–Hartwig coupling was developed and optimised.

    4. Ruthenium Nanocatalysts

      Synthesis of Chiral Functionalised Cyclobutylpyrrolidines and Cyclobutylamino Alcohols from (–)-(S)-Verbenone – Applications in the Stabilisation of Ruthenium Nanocatalysts

      Jordi Aguilera, Isabelle Favier, Marta Sans, Àlex Mor, Ángel Álvarez-Larena, Ona Illa, Montserrat Gómez and Rosa M. Ortuño

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403176

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      Pyrrolidines and amino alcohols anchored to chiral polysubstituted cyclobutane moieties are synthesised stereoselectively from (–)-verbenone. Some of them are appropriate stabilisers of ruthenium nanoparticles and find catalytic applications in the hydrogenation of arenes and nitrobenzene derivatives to afford selectively the corresponding cyclohexane or aniline derivatives.

    5. Synthetic Methods

      Stereoselective TiCl4-Mediated Aldol Reactions Starting from Acylsilanes

      Gangababu Marri, J. Satyanarayana Reddy, Johal Ruiz, Saibal Das and René Grée

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403263

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      A new, simple and efficient method has been developed for the preparation of β-hydroxyacylsilanes through a Lewis acid mediated aldol condensation. The use of TiCl4 under optimized reaction conditions allows the preparation of the target molecules in fair-to-good yields with excellent syn selectivities.

    6. Isoindole Synthesis

      Synthesis of Isoindoles by One-Electron Reductions of Dibenzo[1,4]diazocines

      Marcel Bovenkerk and Birgit Esser

      Article first published online: 16 DEC 2014 | DOI: 10.1002/ejoc.201403315

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      A protocol for the synthesis of isoindoles through one-electron reductions of dibenzo[1,4]diazocines is reported. Six novel isoindole derivatives have been synthesized, and the reaction mechanism has been studied by 1H NMR spectroscopy and quantum chemical calculations.

    7. Directed Metalation

      Directed Functionalization of Halophenyl-2-oxazolines with TMPMgCl·LiCl

      João H. C. Batista, Fernanda M. dos Santos, Leandro A. Bozzini, Ricardo Vessecchi, Alfredo R. M. Oliveira and Giuliano C. Clososki

      Article first published online: 15 DEC 2014 | DOI: 10.1002/ejoc.201403255

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      An efficient protocol was developed for the regioselective synthesis of difunctionalized aryl-2-oxazolines by employing the base TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) in a directed metalation that takes place at room temperature followed by the addition of various electrophiles. The method allows for the isolation of the desired products in good yields.

    8. Dehalogenation of Diiodoalkenes

      Mechanism and Scope of the Base-Induced Dehalogenation of (E)-Diiodoalkenes

      Daniel Resch, Chang Heon Lee, Siew Yoong Tan, Liang Luo and Nancy S. Goroff

      Article first published online: 15 DEC 2014 | DOI: 10.1002/ejoc.201402992

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      A diiodoalkene diester undergoes hydrolysis on treatment with KOH, but eliminates iodine on reaction with iodide salts. This orthogonal reactivity is just one example of the interesting chemistry that arises from the reactions of diiodoalkenes with Lewis bases. The mechanism for this mild reaction has been studied experimentally.

    9. Polycycles

      Controlled Regioselective Amination of Peryleneimides

      Lijo George, Zafar Ahmed, Helge Lemmetyinen and Alexander Efimov

      Article first published online: 12 DEC 2014 | DOI: 10.1002/ejoc.201403299

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      An efficient and direct protocol for the highly regioselective amination of peryleneimides has been developed. The method involves the stepwise formation of a radical anion, which is then oxidized in situ under mild reaction conditions.

  2. Short Communications

    1. Polycyclic Amines

      Synthesis of Polycyclic Amines through Mild Metal-Free Tandem Cross-Dehydrogenative Coupling/Intramolecular Hydroarylation of N-Aryltetrahydroisoquinolines and Crotonaldehyde

      Xiang Wu, Dian-Feng Chen, Shu-Sen Chen and Yi-Fan Zhu

      Article first published online: 12 DEC 2014 | DOI: 10.1002/ejoc.201403375

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      Tandem oxidative cross-dehydrogenative coupling/intramolecular hydroarylation between N-aryltetrahydroisoquinolines and crotonaldehyde enables the rapid construction of ring-fused tetrahydroquinolines. The first metal-free catalytic oxidative coupling of γ-selective C(sp3)–H bonds of crotonaldehyde is realized by using a secondary amine catalyst and 2,3-dichloro-5,6-dicyanoquinone (DDQ).

  3. Full Papers

    1. C–F Bond Functionalization

      Transition-Metal-Free Synthesis of Fluorinated Nitriles and Diaryl Ketones Through a Selective C–F Bond Functionalization Under Mild Conditions

      Guang-Hui Yang, Ming Liu, Na Li, Ran Wu, Xu Chen, Ling-Ling Pan, Shang Gao, Xing Huang, Chen Wang and Chuan-Ming Yu

      Article first published online: 12 DEC 2014 | DOI: 10.1002/ejoc.201403354

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      A highly efficient and simple procedure was developed to synthesize substituted fluorinated nitriles and diaryl ketones under mild conditions from polyfluorobenzenes and phenylacetonitriles. This coupling process proceeded through a selective C–F bond functionalization without the use of a transition-metal catalyst and afforded the products in moderate to excellent yields.

    2. Enzymatic Sulfation

      Enzymatic Sulfation of Phenolic Hydroxy Groups of Various Plant Metabolites by an Arylsulfotransferase

      Michael A. van der Horst, Aloysius F. Hartog, Rabab El Morabet, Arthur Marais, Menzo Kircz and Ron Wever

      Article first published online: 12 DEC 2014 | DOI: 10.1002/ejoc.201402875

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      Sulfation of phenols is usually carried out chemically or using PAPS-dependant sulfotransferases. We show here that a bacterial arylsulfotransferase easily and selectively sulfates a variety of (poly)phenols, e.g., E-resveratrol, phloretin, and quercitin, using cheap p-nitrophenyl sulfate as a donor.

    3. Chirality

      Inherently Chiral Calix[5]arenes Incorporating an Axially Chiral Binaphthyl Moiety: Synthesis, Structures and Chiral Recognition

      Wen-Zhen Zhang, Ke Yang, Si-Zhe Li, Hui Ma, Jun Luo, Kai-Ping Wang and Wen-Sheng Chung

      Article first published online: 12 DEC 2014 | DOI: 10.1002/ejoc.201403298

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      Regioselective monoalkylation of 1,3-calix[5]crown-6 incorporating an axially chiral BINOL moiety produced readily separable, inherently chiral diastereomers.

  4. Short Communications

    1. Nitrogen Heterocycles

      Copper(I)-Catalyzed One-Pot Synthesis of Highly Functionalized Pyrrolidines from Sulfonyl Azides, Alkynes, and Dimethyl 2-(Phenylamino)maleate

      Devenderan Ramanathan and Kasi Pitchumani

      Article first published online: 12 DEC 2014 | DOI: 10.1002/ejoc.201403285

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      A cascade process involving a copper-catalyzed azide–alkyne [3+2] cycloaddition/ring rearrangement/ketenimine formation/intermolecular nucleophilic addition sequence and consequent intramolecular cyclization followed by [1,3]-H shift is reported.

  5. Corrections

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  6. Microreviews

    1. Artificial Oxygenases

      Artificial Flavin Systems for Chemoselective and Stereoselective Oxidations

      Radek Cibulka

      Article first published online: 11 DEC 2014 | DOI: 10.1002/ejoc.201403275

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      This review covers the design and applications of artificial flavinium-based organocatalytic systems for chemoselective and stereoselective oxygenations with hydrogen peroxide and oxygen as stoichiometric oxidising agents.

  7. Full Papers

    1. Natural Products

      Absolute Configurations of Melanoxadin, MR-93A, Melanoxazal, and MR-93B

      Tian-Jun He, Shijun Zhu, Xiao-Wei Lu, Yikang Wu and Yan Li

      Article first published online: 11 DEC 2014 | DOI: 10.1002/ejoc.201403287

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      The title compounds were isolated from Trichoderma sp. in the mid-1990s, and their planar structures were established by spectroscopic means. However, information on the configurations has been missing, unavoidably created lasting uncertainty about the molecular identity of these bioactive oxazoles, especially when some of the reported optical rotation data were incorrect. Here we address these stereochemistry questions.

    2. Phthalocyanines

      1,2,5-Chalcogenadiazole-Annulated Tripyrazinoporphyrazines: Synthesis, Spectral Characteristics, and Influence of the Heavy Atom Effect on Their Photophysical Properties

      Jan Svec, Petr Zimcik, Lucie Novakova, Oleg A. Rakitin, Stanislav A. Amelichev, Pavel A. Stuzhin and Veronika Novakova

      Article first published online: 11 DEC 2014 | DOI: 10.1002/ejoc.201403329

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      The effect of the introduction of different chalcogendiazole rings into porphyrazine analogues is discussed from the point of view of the Q-band position, quantum yields of fluorescence emission, and singlet oxygen production. The successful synthesis of the target low-symmetry zinc, magnesium, and metal-free macrocycles is described. The formation of an unexpected product is also noted.

    3. Asymmetric Catalysis

      Preparation and Catalytic Activity of BINOL-Derived Silanediols

      Joshua M. Wieting, Thomas J. Fisher, Andrew G. Schafer, Michael D. Visco, Judith C. Gallucci and Anita E. Mattson

      Article first published online: 11 DEC 2014 | DOI: 10.1002/ejoc.201403441

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      A family of BINOL-derived enantiopure silanediols has been prepared and studied. The effect of the substitution pattern of the BINOL backbone on catalyst performance is detailed. The acidities and chloride binding constants are also reported for this new and exciting class of hydrogen-bond donor (HBD) catalysts.

    4. Radical Design

      Designing Stable Radicals with Highly Electrophilic or Nucleophilic Character: Thiadiazinyl as a Case Study

      Freija De Vleeschouwer, Artiom Chankisjijev, Paul Geerlings and Frank De Proft

      Article first published online: 11 DEC 2014 | DOI: 10.1002/ejoc.201403198

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      Inverse molecular design has revealed that the thiadiazinyl structure can be made moderately nucleophilic or highly electrophilic depending on the electronic character of its substituents. Under the additional condition of being stable, the electrophilicity optimum shows a significant drop from highly to merely moderately electrophilic.

    5. Organocatalysis

      Applied Enantioselective Aminocatalysis: α-Heteroatom Functionalization Reactions on the Carbapenem (β-Lactam Antibiotic) Core

      Zamani E. D. Cele, Per I. Arvidsson, Hendrik G. Kruger, Thavendran Govender and Tricia Naicker

      Article first published online: 11 DEC 2014 | DOI: 10.1002/ejoc.201403238

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      A carbapenem intermediate serves as a useful nucleophile in organocatalyst-mediated α-heterofunctionalization reactions leading to the formation of diverse products.

    6. Regioselective Synthesis

      Regioselective Synthesis of 1,3- and 1,2-Tocopheryl Glyceride Ethers of Carboxylic Acids

      Bo Seul Choi, Jeongae Choi, Seonyoung Bak and Sangho Koo

      Article first published online: 11 DEC 2014 | DOI: 10.1002/ejoc.201403267

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      Bu4NBr-catalyzed regioselective acidolysis of α-tocopheryl glycidyl ether and selective reduction of acetate by LiEt3BH at –78 °C allowed the regioselective preparation of 1,3- and 1,2-tocopheryl glyceride ethers.

  8. Short Communications

    1. Carbon Dioxide Utilization

      Selective Formation of Trimethylene Carbonate (TMC): Atmospheric Pressure Carbon Dioxide Utilization

      Benjamin R. Buckley, Anish P. Patel and K. G. Upul Wijayantha

      Article first published online: 10 DEC 2014 | DOI: 10.1002/ejoc.201403385

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      The first atmospheric pressure carbon dioxide incorporation into oxetane to selectively form trimethylene carbonate (TMC) is reported. This is a significant challenge since TMC is thermodynamically less favoured than its corresponding co-polymer. This system is capable of converting a 3,3-substituted oxetane to the corresponding cyclic carbonate in good yield.

    2. Arylation

      Desulfitative C-Arylation of Glycals by Using Benzenesulfonyl Chlorides

      Anil Kumar Kusunuru, Syed Khalid Yousuf, Madhubabu Tatina and Debaraj Mukherjee

      Article first published online: 10 DEC 2014 | DOI: 10.1002/ejoc.201403195

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      A highly stereoselective desulfitative C-arylation reaction is developed by using glycal and arylsulfonyl chlorides in the presence of bis(triphenylphosphine)palladium(II) chloride and Li2CO3. A wide variety of glycals and arylsulfonyl chlorides participate in the reaction smoothly. C-Arylation happens possibly through a catalytic cycle involving PdII/Pd0 species.

  9. Full Papers

    1. Isotopic Labelling

      Convenient Synthesis of Diaryliodonium Salts for the Production of [18F]F-DOPA

      Richard Edwards, Andrew D. Westwell, Stephen Daniels and Thomas Wirth

      Article first published online: 9 DEC 2014 | DOI: 10.1002/ejoc.201403378

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      A simple protocol has been developed leading to bench-stable, complex iodonium precursors for the synthesis of [18F]F-DOPA.

    2. Chiral Resolution

      Convenient Chemoenzymatic Route to Optically Active β-Aryl-δ-iodo-γ-lactones and β-Aryl-γ-iodo-δ-lactones with the Defined Configurations of Stereogenic Centers

      Witold Gładkowski, Andrzej Skrobiszewski, Marcelina Mazur, Monika Siepka and Agata Białońska

      Article first published online: 9 DEC 2014 | DOI: 10.1002/ejoc.201403343

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      Iodolactones substituted at the β-position with a phenyl or 4-methylphenyl ring have been synthesized in both enantiomeric forms. Starting materials were allyl alcohols, which were resolved by a lipase-catalyzed transesterification process. The configurations of the iodolactones were either established by X-ray analysis or predicted on the basis of the iodolactonization mechanism.

    3. Gangliosides

      Total Synthesis of Sulfated Glycosphingolipid SM1a, a Kind of Human Epithelial Carcinoma Antigen

      Pengtao Zhang, Kun Wang, Jun Zhang, Chunxia Li and Huashi Guan

      Article first published online: 9 DEC 2014 | DOI: 10.1002/ejoc.201403296

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      An endogenous sulfoglycolipid from mammalian kidney, SM1a, has been synthesized. A [3+2] convergent approach to the target molecule was used. Coupling of the trisaccharide containing a potential sulfation site with a cyclic glucosyl ceramide (GlcCer) unit gave the backbone structure of SM1a, which was converted into ganglioside SM1a after selective sulfonation and global deprotection.

    4. Synthetic Methods

      Copper-Catalyzed Cross-Coupling of Thiols, Alcohols, and Oxygen for the Synthesis of Esters

      Seungyeon Lim, Miran Ji, Xi Wang, Chan Lee and Hye-Young Jang

      Article first published online: 8 DEC 2014 | DOI: 10.1002/ejoc.201403311

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      Copper-catalyzed coupling of thiols, alcohols, and oxygen provided a variety of esters through S/O exchange of thionoester intermediates

    5. Spiro Compounds

      A General and Efficient Method to Access Tetracyclic Spirooxindole Derivatives

      Abderrahman El Bouakher, Stéphane Massip, Christian Jarry, Yves Troin, Isabelle Abrunhosa-Thomas and Gérald Guillaumet

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201403292

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      Tetracyclic spirooxindoles were easily prepared from N-protected isatins and 2-fluoropyridine, leading to fused C-3 oxindole heterocycles in good yields.

  10. Short Communications

    1. Fluorophores

      Design and Characterization of 4,5-Bis(diarylamino)phthalic Acid Diesters as a New Class of Fluorophores Exhibiting Efficient Blue Emission in the Solid State

      Masaki Shimizu and Tomokazu Tamagawa

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201403272

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      Diorgano 4,5-bis(diarylamino)phthalates exhibited blue fluorescence in solution and in the solid state with good efficiency. The emission spectra were finely shifted by changing the substituents in the para positions of each phenyl group of the diarylamino moieties as well as the carbonaceous moieties of the alkoxycarbonyl groups.

    2. Vinyl Sulfones

      CuSO4·5H2O-H-Phosphonate-Catalyzed Intermolecular C–S Bond Formation: Synthesis of (E)-Vinyl Alkylsulfones from Alkynes­ and DMSO

      Jian-Yu Chen, Xiao-Lan Chen, Xu Li, Ling-Bo Qu, Qing Zhang, Li-Kun Duan, Ying-Ya Xia, Xin Chen, Kai Sun, Zhi-Dong Liu and Yu-Fen Zhao

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201403278

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      A novel and efficient CuSO4·5H2O-H-phosphonate-catalyzed synthesis of (E)-vinyl alkylsulfones from alkynes and widely available DMSO was developed.

    3. Cyclophane Phenols and Quinones

      Synthesis of Bromo-Substituted 4-Hydroxy[2.2]paracyclophanes and [2.2]Paracyclophane-4,7-quinones as Versatile Chiral Building Blocks

      Natalia V. Atman (Vorontsova), Roman P. Zhuravsky, Dmitrii Yu. Antonov, Elena V. Sergeeva, Ivan A. Godovikov, Zoya A. Starikova and Anna V. Vologzhanina

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201403316

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      The syntheses of a number of mono- and disubstituted 4-hydroxy[2.2]paracyclophanes and substituted [2.2]paracyclophane-4,7-quinones with various substitution patterns are elaborated. The planar chiral building blocks combine bromine atoms, hydroxy groups, and/or quinoid fragments in their structures, and they are ready for further transformations (including resolution into enantiomers).

    4. Hydrogenation

      Ruthenium-Catalyzed Conjugate Hydrogenation of α,β-Enones by in situ Generated Dihydrogen from Paraformaldehyde and Water

      Wanfang Li and Xiao-Feng Wu

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201403359

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      Dihydrogen (H2) is produced from paraformaldehyde and water in the presence of simple RuCl2(PPh3)3 as a catalyst. The in situ generated hydrogen is utilized in the selective hydrogenation of olefins in α,β-enones catalyzed by the same catalyst. This high-pressure-free procedure shows very high selectivity and generality.

    5. Oligonucleotides

      Solid-Phase Synthesis of Oligonucleotide 5′-(α-P-Thio)triphosphates and 5′-(α-P-Thio)(β,γ-methylene)triphosphates

      Yann Thillier, Corinne Sallamand, Carine Baraguey, Jean-Jacques Vasseur and Françoise Debart

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201403381

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      The first synthesis of oligonucleotides (ONs) 5′-functionalized with a (α-P-thio)triphosphate moiety is reported. Subsequent ON assembly, 5′-H-phosphonylation, thiooxidation, activation to phosphoanhydride, and then pyrophosphate or its β,γ-methylene analogue substitution are achieved on a solid support in good yields. These original hydrolysis-resistant 5′-triphosphate ONs will be useful in biological research.

    6. Photocatalysis

      Photocatalytic α-Oxyamination of Stable Enolates, Silyl Enol Ethers, and 2-Oxoalkane Phosphonic Esters

      Peter Schroll and Burkhard König

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201403433

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      Fast and efficient visible-light-mediated α-oxyamination of β-keto enolates, silyl enol ethers, and deprotonated dialkyl 2-oxoalkanephosphonates occurs in a microreactor in the presence of [Ru(bpy)3]2+ (bpy = 2,2′-bipyridyl) as a photocatalyst, 2,2,6,6-tetramethylpiperidine nitroxide (TEMPO), and blue light. The key step is the light-induced one-electron oxidation of TEMPO.

    7. Natural Products

      Isolation and Structure Elucidation of Hyperibine J [Revised Structure of Adhyperfirin (7-Deprenyl-13-methylhyperforin)]: Synthesis of Hyperibone J

      Kornilia P. Mitsopoulou, Veroniki P. Vidali, Anna Maranti and Elias A. Couladouros

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201403264

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      Structure elucidation of hyperibine J, a new polycyclic polyprenylated acylphloroglucinol isolated from Hypericum sp., is described. Molecular weight and spectroscopic data comparison with adhyperfirin (7-deprenyl-13-methylhyperforin) declared a structure revision of the latter. Hyperibine J is very similar to hyperforin and possesses a methyl substituent instead of a prenyl group at C-1; mCPBA = meta-chloroperoxybenzoic acid.

  11. Microreviews

    1. Enantioenriched Organophosphorus Compounds

      Organocatalytic Synthesis of Optically Active Organophosphorus Compounds

      Marek Dzięgielewski, Jakub Pięta, Elżbieta Kamińska and Łukasz Albrecht

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201403184

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      Organophosphorus reagents play pivotal roles in modern organic synthesis and have found many applications for the preparation both of synthetically important compounds and of biologically relevant ones. They are now widely employed in asymmetric organocatalysis to afford optically active organophosphorus compounds. This review summarizes recent progress in this field of enantioselective synthesis.

  12. Full Papers

    1. Synthetic Methods

      Trimethylsilyl Iodide Mediated One-Pot Synthesis of 2-Allyl-2H-chromenes

      Birakishore Padhi, D. Srinivas Reddy and Debendra K. Mohapatra

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201403240

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      A one-pot metal-free trimethylsilyl iodide (TMSI) mediated method for the synthesis of 2-allyl-2H-chromenes has been developed. The reaction uses commercially available, inexpensive starting materials in a simple procedure that takes place under mild conditions. It is significant that sensitive functional groups on the aromatic ring of the substrate are not affected by the reaction conditions.

    2. Luminscent Compounds

      Synthesis, Characterisation, and Electroluminescence Properties of N-Coumarin Derivatives Containing Peripheral Triphenylamine

      Palita Kotchapadist, Narid Prachumrak, Thitiya Sunonnam, Supawadee Namuangruk, Taweesak Sudyoadsuk, Tinnagon Keawin, Siriporn Jungsuttiwong and Vinich Promarak

      Article first published online: 5 DEC 2014 | DOI: 10.1002/ejoc.201402680

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      N-Coumarin derivatives (CThn and CThnC) show good film-forming ability, high thermal stability, and photoluminescence properties. The solution-processed OLEDs using these coumarins as the emissive layer display green to orange colours with the maximum power efficiencies up to 1.62 lm W–1 at 13.0 V.

    3. Rotaxanes

      Preparation of Pillar[5]arene-Based [2]Rotaxanes from Acyl Chlorides and Amines

      Radian Milev, Alberto Lopez-Pacheco, Iwona Nierengarten, Thi Minh Nguyet Trinh, Michel Holler, Robert Deschenaux and Jean-François Nierengarten

      Article first published online: 4 DEC 2014 | DOI: 10.1002/ejoc.201403380

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      The yields of pillar[5]arene-based [2]rotaxanes from the reactions of diacyl chloride reagents with various amine stoppers are sensitive to the reaction conditions (solvent and stoichiometry) as well as to structural and electronic factors.

    4. Radical Coupling

      Radical Titanocene Promoted Coupling of Epoxides and Vinyl Sulfones

      Alfonso Fernández-Mateos, Soledad Encinas-Madrazo, Pablo Herrero-Teijón and Rosa Rubio González

      Article first published online: 4 DEC 2014 | DOI: 10.1002/ejoc.201403288

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      A radical coupling reaction of vinyl sulfones and epoxides was mediated by Cp2TiCl (Cp = cyclopentadienyl) to provide straightforward synthetic access to hydroxy sulfones. The reaction was achieved by using either an excess or a catalytic amount of the TiIII reagent. The scope of the reaction was studied for several different substituted epoxides and vinyl sulfones.

    5. Multicomponent Reactions

      ZnCl2-Promoted One-Pot Three-Component Synthesis of Multisubstituted Thiazolo[4,5-b]pyridines and Thieno[2,3-b:4,5-b′]dipyridines

      Laichun Luo, Lanlan Meng, Yangqiu Peng, Yongning Xing, Qi Sun, Zemei Ge and Runtao Li

      Article first published online: 4 DEC 2014 | DOI: 10.1002/ejoc.201403156

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      A facile ZnCl2-promoted one-pot three-component synthesis of thiazolo[4,5-b]pyridines and thieno[2,3-b:4,5-b′]dipyridines is described. This approach involves a tandem SN2/Thorpe–Ziegler cyclization/Friedländer reaction to give fused pyridines in moderate to good yields.

    6. Odour Compounds

      Synthesis of Saturated Benzodioxepinone Analogues: Insight into the Importance of the Aromatic Ring Binding Motif for Marine Odorants

      Christopher M. Plummer, Robert Gericke, Philip Kraft, Aaron Raynor, Jordan Froese, Tomáš Hudlický, Trevor J. Rook, Oliver A. H. Jones and Helmut M. Hügel

      Article first published online: 4 DEC 2014 | DOI: 10.1002/ejoc.201403142

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      As part of our research exploring the influence of molecular variations of Calone 1951® on marine fragrance performance, we report the synthesis, crystal structures, and olfactory analysis of the first saturated benzodioxepinone analogues. Our results showed that an aromatic ring system is necessary for binding to the marine odour receptor(s).

  13. Short Communications

    1. Michael Addition

      Highly Enantioselective Michael Addition of 2-Fluoro-1,3-diketones to Nitroalkenes

      Jacek Kwiatkowski and Yixin Lu

      Article first published online: 2 DEC 2014 | DOI: 10.1002/ejoc.201403361

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      The asymmetric synthesis of fluorinated 1,3-diketones is achieved through quinine–sulfonamide mediated asymmetric Michael addition of racemic 2-fluoro-1,3-diketones to nitroalkenes. Subsequent stereoselective reduction of the carbonyl groups led to a functionalized fluoroisostere of the triol and generation of four stereogenic carbon centers, including one quaternary center, in two reaction steps.

    2. Organocatalysis

      Organocatalytic α-Addition of Isocyanides to Aldehydes

      Takeshi Yamada, Tomoyasu Hirose, Satoshi Ōmura and Toshiaki Sunazuka

      Article first published online: 2 DEC 2014 | DOI: 10.1002/ejoc.201403313

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      3,5,6-Trifluoro-2-pyridone is an efficient catalyst for the α-addition of isocyanides to aldehydes in the presence of water in benzene. Various aldehydes and isocyanides performed well in this reaction to provide the α-hydroxyamides. Even highly constrained substrates were well tolerated. This is the first example of pyridone-catalyzed α-addition of isocyanides.

  14. Full Papers

    1. Nucleosides

      Synthesis and Stability of Nucleoside 3′,5′-Cyclic Phosphate Triesters Masked with Enzymatically and Thermally Labile Phosphate Protecting Groups

      Vyankat A. Sontakke, Vaishali S. Shinde, Harri Lönnberg and Mikko Ora

      Article first published online: 2 DEC 2014 | DOI: 10.1002/ejoc.201403227

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      Nucleoside 3′,5′-cyclic phosphotriesters that bear 3-acetyloxy-2,2-bis(ethoxycarbonyl)propyl, 4-acetylthio-2,2-dimethyl-3-oxobutyl, and 4-(tert-butyldisulfanyl)-2,2-dimethyl-3-oxobutyl groups were prepared. Their conversion into cyclic phosphodiesters at pH 7.5 and 37 °C in the presence and absence of enzyme was monitored by reverse-phase HPLC.

  15. Microreviews

    1. Frondosin Natural Products

      The Frondosins: An Unusual Synthetic and Stereochemical Journey

      Michael D. VanHeyst and Dennis L. Wright

      Article first published online: 28 NOV 2014 | DOI: 10.1002/ejoc.201403116

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      The first two syntheses of (+)-frondosin B, by Danishefsky and by Trauner, gave conflicting assignments for the single stereocenter at C8. Ensuing syntheses of frondosins B and A resolved this conflict and established that (+)-frondosin B is the R enantiomer. Wright's group showed that a late-stage stereochemical inversion occurred in a common intermediate of both their and Trauner's syntheses.

  16. Full Papers

    1. Amide Formation

      Iron/Caffeine as a Catalytic System for Microwave-Promoted Benzamide Formation

      Xavier Bantreil, Pauline Navals, Jean Martinez and Frédéric Lamaty

      Article first published online: 28 NOV 2014 | DOI: 10.1002/ejoc.201403173

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      Upon microwave activation, benzamides were formed directly from alcohols and amines in yields up to 84 % and TOFs (turnover frequencies) up to 33.6 h–1. Among the examined transition metals, only nontoxic and inexpensive FeCl2·4H2O along with caffeine as a stabilizing ligand provided the uniquely efficient catalytic system for the benzamide formation.

    2. C–H Functionalization

      Ceric Ammonium Nitrate (CAN) Promoted PdII-Catalyzed Substrate-Directed o-Benzoxylation and Decarboxylative o-Aroylation

      Sourav Kumar Santra, Arghya Banerjee, Nilufa Khatun and Bhisma K. Patel

      Article first published online: 27 NOV 2014 | DOI: 10.1002/ejoc.201403367

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      CAN can activate: Inexpensive ceric ammonium nitrate (CAN) is an efficient oxidant for the Pd-catalyzed substrate-directed o-benzoxylation and decarboxylative o-aroylation processes. In the presence of CAN, the reaction of directing arenes with carboxylic acids resulted in o-benzoxylated products, and that with α-keto acids led to the formation of o-aroylation products.

    3. IrIII-Catalyzed Direct C-7 Amidation of Indolines with Sulfonyl, Acyl, and Aryl Azides at Room Temperature

      Wei Hou, Yaxi Yang, Wen Ai, Yunxiang Wu, Xuan Wang, Bing Zhou and Yuanchao Li

      Article first published online: 27 NOV 2014 | DOI: 10.1002/ejoc.201403355

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      An IrIII-catalyzed C-7 selective C–H amidation of indolines with organic azides has been achieved. This method offers an environmentally benign, readily scalable synthesis for 7-aminoindolines. More importantly, acyl, sulfonyl, and aryl azides can be employed in this C–H amidation reaction under very mild reaction conditions (DCE = 1,2-dichloroethane).

    4. Asymmetric Synthesis

      Synthesis of (+)-6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid, a Diastereoselective Approach

      Ilona Bułyszko, Maria Chrzanowska, Agnieszka Grajewska and Maria D. Rozwadowska

      Article first published online: 27 NOV 2014 | DOI: 10.1002/ejoc.201403218

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      The total synthesis of (+)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid involves a combination of two synthetic strategies, that is, the Petasis synthesis of amino acids and the Pomeranz–Fritsch–Bobbitt synthesis of tetrahydroisoquinoline derivatives. Chiral aminoacetaldehyde acetals were used as building blocks and to direct the stereochemistry of this synthesis.

    5. Dyes for Microscopy

      Functionalization of the meso-Phenyl Ring of Rhodamine Dyes Through SNAr with Sulfur Nucleophiles: Synthesis, Biophysical Characterizations, and Comprehensive NMR Analysis

      Gyuzel Yu. Mitronova, Svetlana Polyakova, Christian A. Wurm, Kirill Kolmakov, Thomas Wolfram, Dirk N. H. Meineke, Vladimir N. Belov, Michael John and Stefan W. Hell

      Article first published online: 26 NOV 2014 | DOI: 10.1002/ejoc.201403269

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      Aromatic nucleophilic substitution of fluorine in 9-(3′-carboxy-4′,5′,6′,7′-trifluorophenyl) groups of xanthene dyes is regioselective (for thiols and amines). The reaction was used for the synthesis of a “bright” and very photostable dye for two-color superresolution microscopy. Characteristics of the NMR spectra may be used for structure elucidation of other fluorescent dyes.

    6. Energetic Materials

      Pentaerythritol-Based Energetic Materials Related to PETN

      Quirin J. Axthammer, Burkhard Krumm and Thomas M. Klapötke

      Article first published online: 25 NOV 2014 | DOI: 10.1002/ejoc.201403265

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      New tetravalent pentaerythritol tetranitrocarbamate (PETNC) and its tetraammonium salt have been synthesized by an efficient two-step synthesis starting from pentaerythritol, the precursor to pentaerythritol tetranitrate (PETN). Their energetic properties are discussed in comparison with PETN.

    7. Ligand- and Base-Free CuII-Mediated Selective S-Arylation of α-Enolic Dithioesters by Chan–Lam Coupling at Room Temperature

      Suvajit Koley, Sushobhan Chowdhury, Tanmoy Chanda, B. Janaki Ramulu, Namrata Anand and Maya Shankar Singh

      Article first published online: 25 NOV 2014 | DOI: 10.1002/ejoc.201403171

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      Ligand- and base-free cross-coupling of arylboronic acids with α-enolic dithioesters mediated by Cu(OAc)2 has been achieved at room temperature under aerobic neutral conditions to yield unsymmetrical α-oxoketene S,S-acetals for the first time. Distinctive features of this novel approach embrace short reaction times (5 min), good yields and highly selective C=S functionalization in one pot.

    8. Carbohydrate Mimetics

      Preparation of Multivalent Carbohydrate Mimetics Based on Enantiopure 1,2-Oxazines by Sonogashira Coupling and Subsequent Reductive Ring-Opening

      Maja Kandziora and Hans-Ulrich Reissig

      Article first published online: 25 NOV 2014 | DOI: 10.1002/ejoc.201403186

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      Modular, flexible, efficient! A series of mono- to tetravalent carbohydrate mimetics with the D-talose configuration have been prepared based on an aminopyran building block. Glaser and Sonogashira coupling reactions were the crucial reactions, followed by reductive steps, either palladium-catalyzed hydrogenolyses or a combination of hydrogenolysis and samarium diiodide promoted reductions.

    9. Unusual Sugars

      Chemical Synthesis of 1-Deoxy-L-fructose and L-Sorbose Through Carbonyl Translocation

      Hsin-Pei Wu, Nai-Yun Hsu, Tai-Ni Lu and Che-Chien Chang

      Article first published online: 25 NOV 2014 | DOI: 10.1002/ejoc.201403196

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      Two rare sugars – 1-deoxy-L-fructose and L-sorbose – were synthesized from inexpensive starting materials by a carbonyl translocation method.

    10. Peptide Synthesis

      The Effect of Counterion and Tertiary Amine on the Efficiency of N-Triazinylammonium Sulfonates in Solution and Solid-Phase Peptide Synthesis

      Beata Kolesinska, Kamil K. Rozniakowski, Justyna Fraczyk, Inga Relich, Anna Maria Papini and Zbigniew J. Kaminski

      Article first published online: 21 NOV 2014 | DOI: 10.1002/ejoc.201402862

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      The structure of the counterion is important in peptide synthesis. Triazine-based sulfonates derived from three tertiary amines and four sulfonic acids with very diverse properties, which yield exactly the same “superactive” triazine ester after activation of the carboxylic function, presented significant differences in stability, tendency to epimerization, coupling rate, yield, and purity of the final products.

    11. Synthetic Methods

      Bis(trimethylsilyl)selenide in the Selective Synthesis of β-Hydroxy, β-Mercapto, and β-Amino Diorganyl Diselenides and Selenides Through Ring Opening of Strained Heterocycles

      Damiano Tanini, Alessandro Degl'Innocenti and Antonella Capperucci

      Article first published online: 21 NOV 2014 | DOI: 10.1002/ejoc.201403015

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      A selective approach to β-hydroxy, β-mercapto, and β-amino dialkyl diselenides and selenides is described through reaction of bis(trimethylsilyl)selenide (HMDSS) with epoxides, thiiranes, and aziridines under suitable reaction conditions. 77Se NMR chemical shifts were measured to verify the selective synthesis of diselenides and selenides.

  17. Microreviews

    1. Asymmetric Organocatalysis

      Isohexides as Versatile Scaffolds for Asymmetric Catalysis

      Mohammed Kadraoui, Thibault Maunoury, Zoubir Derriche, Stéphane Guillarme and Christine Saluzzo

      Article first published online: 17 NOV 2014 | DOI: 10.1002/ejoc.201402851

      Thumbnail image of graphical abstract

      Two series of dianhydrohexitol derivatives, the first preserving the original bis-fused THF backbones and the second originating from single THF ring-opening reactions, are used as asymmetric ligands in organometallic catalysis or as asymmetric organocatalysts. Their synthesis and their application in different asymmetric reactions for the formation of C–H, C–C, C–N, and C–S bonds are discussed.

    2. [2+2+2] Cycloaddition

      Recent Advances in Stereoselective [2+2+2] Cycloadditions

      Muriel Amatore and Corinne Aubert

      Article first published online: 21 OCT 2014 | DOI: 10.1002/ejoc.201403012

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      [2+2+2] Cycloaddition reactions have achieved a leading position among the available tools for the construction of complex polycyclic molecules. The related asymmetric versions, now giving access to all chirality modes, are obviously more advantageous for the synthetic chemist. This review covers the recent advances in this field.

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